Matchmaker, Matchmaker... Hoping To Stave Off the Valentine’s Day Blues, the Hapless Jewish Writer Seeks Professional Help

Valentine’s Day can summon terrible sadness in Hapless Jews. Last Valentine’s Day, the Hapless Jewish Writer spent the day despairing over his ex.

The Hapless Jewish Writer’s girlfriend ended their relationship at an Indian restaurant December 7 — a date that will live in infamy.

“I love you,” his treacherous blonde-haired vixen declared. “I’m just not in love with you.”

Now that’s cold.

In fact they were the exact same words that Elizabeth Shue said to Woody Allen in “Deconstructing Harry” — a film that the HJW and his girlfriend had watched a few weeks earlier.

“She couldn’t come up with something more original?” the HJW thought as he stared angrily at his linen napkin.

The HJW and his girl would reconcile briefly, but it was not to last. And he fell into an extreme depression. When he stayed home he sobbed into his pillow. When he left his apartment he drank himself to drunkenness, passing out on friends’ floors. He would hold the Barneys necktie that she gave him for his birthday in his hands as if it were a relic from the Second Temple. He begged friends for advice on how to win her back; they told him to move on. His mother recommended that he see a psychiatrist.

And as often happens during the great calamities of his life, the HJW felt the tug of his ancestry and civilization. In moments of despair the HJW fantasized about returning to the religious, shtetly life that his great-grandparents abandoned when they landed on these shores.

So it almost seemed like providence when, in the middle of his crisis, a PR agent contacted the HJW and suggested that he write a story about Shoshanna, the Jewish matchmaker — and use himself as a test case for her matchmaking gifts.

“Sure,” the HJW said. Maybe a good Old World Jewish match was all he really needed.

Known professionally as Shoshanna, Shoshanna Rikon works out of a small office on New York City’s Fifth Avenue, which she shares with her assistant, Melissa. And if the HJW was expecting a bent-over little Jewish woman with a kerchief wrapped around her hair, he was in for a surprise. Shoshanna is a tall, brunet Staten Island native with a brusque, no-nonsense New York manner.

For a mere $700, Shoshanna arranges a dozen dates for her clients during a 12-month period.

Many of the 30-somethings and 40-somethings who visit Shoshanna are sent there by their mothers. “It’s awkward to join the service,” Shoshanna told the HJW. In an uncompromising quest for grandchildren, mothers nudge their adult children along. (“You know,” one of the mothers told Shoshanna, “I’m [your] only competition.”)

“So what are you looking for?” Shoshanna asked the HJW.

“Someone nice,” he said.

“What about looks?” Shoshanna asked.

“Well, it’s important.”

“Is weight important?”

“What do you mean?”

“Well,” Shoshanna said, “we have very pretty girls who are heavy. I mean, not so heavy that you can’t get your arms around them, but….”

He would prefer someone who is not fat, the HJW said. (He felt shallow and guilty for the rest of the day. Oh, how shallow and empty to… whatever.)

The HJW was sent home and told that Melissa would call him with possible dates.

Melissa called him a few days later and swore up and down that number one was a looker. She worked at a magazine, and Melissa was confident that the two of them would hit it off. (“Melissa does that [with] everybody,” Shoshanna said later. “She sees the good in them… I’m the one who’s the honest one. I say, ‘No! That guy’s dead ugly.’”)

The HJW and number one made a date to meet each other at a coffee shop near the HJW’s office, but she called to cancel. She also told him that she was going to be out of town — recovering from an operation — for the next month.

It was too elaborate an excuse to be a lie, the HJW reasoned. She couldn’t have heard about his past already….

But number one and the HJW were not destined to cross paths. A month later, the HJW left a message on her machine, wishing her well and hoping that she had recovered. But number one phoned Melissa and said that she thought the HJW sounded too young. (She was a year older.)

On to number two.

It was a pleasant enough date. The two met at a bar on the Upper West Side near number two’s house, ordered several weird, fruity drinks and spent the next two hours talking about restaurants and a few small towns in Israel that they both knew. The HJW left the date confident enough to ask out number two again. She accepted.

A day or two later, the HJW found a message on his machine saying that upon reflection, she, too, thought he was too young. “I hope we can be friends — if you want,” number two said, and her voice trailed off.

The HJW had very little in common with number three. They met for drinks at the Algonquin Hotel, and the HJW found himself struggling to find things to talk about. He was happy to hear that she, too, disliked the movie “The Matrix,” but that was the high point of the conversation.

Number four and the HJW played phone tag on their answering machines for about a week. After the message swapping had gone on for a few days, the HJW came home and discovered a message from Melissa.

“I don’t mean to sound like a Jewish mother, here,” Melissa began — always the sign of a bad conversation.

During the course of the rest of her message, the HJW loosened his tie, removed his shirt, washed his face and changed his clothes. When he came back to his machine, Melissa was still speaking.

“She’s really a great girl. I really think you’ll hit it off.”

Translation: Don’t blow it by not calling her back.

Finally the HJW and number four met, and had a pleasant enough date. Later, the HJW was more than a little surprised to hear number four’s analysis:

1) The HJW was dorky looking. (The HJW wore glasses.)

2) His hair was too bushy. (The HJW always wore a red Jewfro with pride.)

3) He was a little out of shape. (That hurt. He had lost 20 pounds after his girlfriend dumped him, and he had kept most of it off. Besides, this chick wasn’t exactly Gwyneth Paltrow.)

The HJW went back to Shoshanna’s office, and Shoshanna shook her head at the women who rejected him. “What I personally like about you is you’re willing to go on the second date,” Shoshanna said. “More people should be like you, [HJW].”

Shoshanna and the HJW spent an hour or two reminiscing about the weird types who had floated in and out of her office throughout the years. There was a fellow who had come in with stains on his shirt and with an overpowering body odor (Shoshanna turned him away, but not before making some helpful hygienic suggestions), and a number of non-Jewish women who came in looking for Jewish husbands.

Shoshanna and the HJW left the office and went to a bar for one of Shoshanna’s matchmaking parties, which she throws every few months.

The HJW milled about the party for roughly an hour, martini in hand, when, on his way to the bathroom, he bumped into a small, munchkinlike woman with blond hair.

Shoshanna leaned over and whispered in his ear, “Talk to her!”

The HJW and his new friend struck up a conversation. And before he left the party he got her number. They started going out.

After his initial glow of enthusiasm died down, however, the HJW remembered all the claustrophobic feelings of an attached man. Number five was warm, kind and intelligent, and after a couple of months the HJW felt very afraid. He would be nervous every time the phone rang. He began thinking up excuses to get himself out of dates. He began acting like, for lack of a better word, a schmuck.

He gathered up his courage and broke up with her.

Like clockwork, Melissa called him a week or two later with another match. But by that time, the HJW was a little tired of matchmaking. He met a gorgeous blond shiksa at a party; the next week they canoodled at a bar, and they have been going out ever since.

The HJW realized that there was more than a hint of drama in his desire to go Old World Jewish shtetly. He’s happy dating his lovely shiksa. But he doesn’t have bad things to say about matchmakers — in the ruthlessness of the New York dating world, we Hapless Jews should try it all.

Max Gross is a writer living in New York, and a frequent contributor to the Forward.

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